Lesser date moth (Batrachedra amydraula) is one of the most serious pests that attack date palm in the Middle East and North Africa. As its larvae feed on fruits and soft immature seeds of date palm to make holes near the fruit calyx to enter the pulp, so that they damage the fruits. Infested fruit becomes dark in about four weeks after the attack, and fruit bunch stops growing. Thus, infested fruit turns into dry and falls to the ground, leading a decreased crop. It is difficult to control the pest by insecticides, because the larvae are inside the pulp. Therefore, biological pest control has been attracting great interest, and the use of a sex pheromone is expected for such biological control.
The sex pheromone of the lesser date moth was identified as a 2:2:1 mixture of (5Z)-5-decen-1-yl acetate, (5Z)-5-decen-1-ol and (4Z,7Z)-4,7-decadien-1-yl acetate (Non Patent Literature 1).
Anat Levi-Zada et al. reports a method for producing (4Z,7Z)-4,7-decadien-1-yl acetate, sex pheromone of the lesser date moth, in which 1-(tetrahydropyranyloxy)-4-pentyne is deprotonated, coupled with 2-pentynyl tosylate in the presence of a copper iodide dimethyl sulfide complex to form 1-(tetrahydropyranyloxy)-4,7-decadiyne, which is further converted, by hydroboration and subsequent protonation, into 1-(tetrahydropyranyloxy)-(4Z,7Z)-4,7-decadiene, which is then subjected to simultaneous deprotection and acetylation of the tetrahydropyranyl group (hereinafter referred to also as “THP group”) (Non Patent Literature 2).